Joke 1: The Smartest Man on the Bus

Three newly convicted men were being transported to prison for the first time. Before boarding the bus, each was allowed to bring one personal item to help pass the long, monotonous days ahead.

As the bus rumbled down the highway, one of the men turned to the other and asked,
“So, what did you bring?”

The second man grinned and proudly pulled out a box of paints and brushes.
“I’m going to paint,” he declared. “Landscapes, portraits, murals on the walls if they let me. By the time I get out, I’ll be the Grandma Moses of Jail.”

“Not bad,” the first man nodded.

He reached into his bag and fanned out a shiny deck of cards.
“I brought cards. Poker, solitaire, gin rummy — I’ll stay busy no matter what.”

They both turned to the third man, who had been sitting quietly, smiling to himself like he knew something they didn’t.

“Well?” they asked. “Why are you so pleased? What did you bring?”

Without a word, he reached into his bag and slowly pulled out… a box of tampons.

The other two blinked.

“…Tampons?” one finally said. “What are you supposed to do with those?”

The third man tapped the side of the box confidently and read aloud from the packaging:

“According to this, I can go horseback riding, swimming, roller-skating, dancing, hiking—”

He looked up with a wide grin.

“Looks like I’m about to have the most active prison sentence in history.”

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Joke 2: The Number System

A man is sent to prison for the first time.

That first night, after lights-out, the cell block falls into darkness. Suddenly, his cellmate walks up to the bars and shouts, “Number twelve!”

The entire cell block erupts in laughter.

A few minutes later, someone else yells, “Number four!”

Again, roaring laughter echoes off the concrete walls.

Confused, the new inmate whispers, “What’s going on?”

His older cellmate chuckles.
“We’ve all been here so long, we know all the same jokes by heart. So instead of telling the whole joke, we just shout the number.”

The new guy nods thoughtfully.

After a few minutes, he walks up to the bars and confidently shouts, “Number twenty-nine!”

The reaction is explosive.

The entire block howls. Men pound the walls. Some are gasping for air, laughing harder than before.

When the noise finally dies down, the bewildered newcomer turns to his cellmate.

“Why did everyone laugh so much harder at mine?”

The old prisoner wipes tears from his eyes and grins.

“Because we’d never heard that one before.”